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Synthesis of 2-aryl and coumarin substituted benzothiazole derivatives

2006; Wiley; Volume: 43; Issue: 5 Linguagem: Inglês

10.1002/jhet.5570430535

1943-5193

Rajesh S. Kenny, Uday C. Mashelkar,

Multicomponent Synthesis of Heterocycles

Journal of Heterocyclic ChemistryVolume 43, Issue 5 p. 1367-1369 Article Synthesis of 2-aryl and coumarin substituted benzothiazole derivatives Rajesh S. Kenny, Rajesh S. Kenny Organic Research Laboratory, Patkar-Varde College of Science, Goregaon (W), Mumbai 400062, IndiaSearch for more papers by this authorUday C. Mashelkar, Uday C. Mashelkar Organic Research Laboratory, Patkar-Varde College of Science, Goregaon (W), Mumbai 400062, IndiaSearch for more papers by this author Rajesh S. Kenny, Rajesh S. Kenny Organic Research Laboratory, Patkar-Varde College of Science, Goregaon (W), Mumbai 400062, IndiaSearch for more papers by this authorUday C. Mashelkar, Uday C. Mashelkar Organic Research Laboratory, Patkar-Varde College of Science, Goregaon (W), Mumbai 400062, IndiaSearch for more papers by this author First published: 13 March 2009 https://doi.org/10.1002/jhet.5570430535Citations: 10AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Abstract A facile and effective method for the synthesis of some benzothiazole derivatives is described. The method involves the action of aryl aldehyde and o-aminothiophenol in acetic acid resulting into in situ formation of the thiol substituted Schiff's base and its cyclization to 2-aryl benzothiazole upon prolonged heating. References 1 M. Lácová, J. Chovancová, O. Hýblová and S. Varkonda, Chem. Pap., 45, 411 (1991). 2 I. Chulák, V. Sutorius and V. Sekerka, Chem. Pap., 44, 131 (1990). 3 E. Kashiyama, I. Hutchinson, M. S. Chua, S. F. Stinson, L. R. Phillips, G. Kaur, E. A. Sausville, T. D. Bradshaw, A. D. Westwell and M. F. Stevens, J. Med Chem., 42 (20), 4172 (1999). 4a T. D. Bradshaw, S Wrigley, D. F. Shi, R. J. Schultz, K. D. Paull and M. F. Stevens, Br J Cancer., 77 (5), 745 (1998); b D. F. Shi, T. D. Bradshaw, S. Wrigley, C. J. McCall, P. Lelieveld, I. Fichtner and M. F. Stevens, J Med Chem., 39 (17), 3375 (1996). 5a T. D. Bradshaw, M. S. Chua, H. L. Browne, V. Trapani, E. A. Sausville, M. F. G. Sevens, Br. J. Cancer., 86, 1348 (2002); b I. Hutchinson, M. S. Chua, H. L. Browne, V. Trapani, T. D. Bradshaw, A. D. Westwell and M. F. Stevens, J Med Chem., 44 (9), 1446 (2001); c M. F. Stevens, C. J. McCall, P. Lelieveld, P. Alexander, A. Richter and D. E. Davies, J. Med. Chem., 37 (11), 1689 (1994). 6a I. Hutchinson, S. A. Jennings, B. R. Vishnuvajjala, A. D. Westwell and M. F. G. Stevens, J. Med. Chem., 45, 744 (2002); b T. D. Bradshaw, M. F. Sevens and A. D. Westwell, Curr Med Chem., 8 (2), 203 (2001); c M. S. Chua, D. F. Shi, S. Wrigley, T. D. Bradshaw, I. Hutchinson, P. N. Shaw, D. A. Barrett, L. A. Stanley and M. F. Stevens, J. Med. Chem., 42 (3), 381 (1999). 7 A. D. Borthwick, D. E. Davies, P. F. Ertl, A. M. Exall, T. M. Haley, G. J. Hart, D. L. Jackson, N. R. Parry, A. Patikis, N. Trivedi, G. G. Weingarten, J. M. Woolven, J. Med. Chem., 46 (21), 4428 (2003). 8 S. R. Nagaraian, G. A. De Crescenzo, D. P. Getman, H. Lu, J. A. Sikorski, J. L. Walker, J. J. McDonald, K. A. Houseman, G. P. Kocan, N. Kishore, P. P. Mehta, C. L. Funkes-Shippy and L. Blystone, Eur. J. Med. Chem., 11, 4769 (2003). 9 I. Yildiz-Oren, I. Yalcin, E. Aki-Sener and N. Ucarturk, Eur. J. Med. Chem., 39 (3), 291 (2004). 10 A. Latrofa, M. Franco, A. Lopedota, A. Rosato, D. Carone and C. Vitali Fermaco, 60 (4), 291 (2005). 11 J. Das, R. V. Moquin, C. Liu, A. M. Doweyko, H. F. Defex, Q. Fang, S. Pang, S. Pitt, D. R. Shan, G. L. Schieven and J. Wityac, Bioorg. Med. Chem. Lett., 13, 2587 (2003). 12 S. J. Hays, M. J. Rice, D. F. Ortwine, G. Johnson, R. D. Schwarz, D. K. Boyd, L. F. Copeland, M. G. Vartanian and P. A. Boxer, J. Pharm. Sci., 83, 1425 (1994). 13 P. Jimonet, F. Audiau, M. Barreau, J. C. Blanchard, A. Boireau, Y. Bour, M. A. Coleno, A. Doble, G. Doerflinger, C. D. Huu, M. H. Donat, J. M. Duchesne, P. Ganil, C. Gueremy, E. Honore, B. Just, R. Kerphirique, S. Gontier, P. Hubert, P. M. Laduron, J. Le Blevec, M. Meunier, J. M. Miquet, C. Nemecek, M. Pasquet, J. P. Pratt, J. Ratuad, M. Reibud, J. M. Stutzman and S. Mignani, J. Med. Chem., 42, 2828 (1999). 14 Y. He, A. Benz, T. Fu, M. Wang, D. F. Covey, C. F. Zorumski and S Mennerick, Neuropharmacology, 42, 199 (2002). 15 G Bensimon, L. Lacomblez. and V. Mienenger, New Engl. J. Med., 35, 295 (1994). 16 C. Y. Jeong, J. Choi and M. Ha Yoon, Eur. J. Pharmacol., 502 (3), 205 (2004). 17a H. Schwartz, Nath Appl., 6, 607, 039, (1966); Chem. Abstr., Vol #, abstract # (year); b A. Osuka, Y. Uno, H. Horiuchi and H. Suzuki, Synthesis, 145 (1984); c H. Saikachi and T. Hisono, Chem. Pharm. Bull., 8, 51 (1960); d S. H. Compare and T. Hisano, Chem. Pharm. Bull., 7, 716 (1959). 18 F. M. Moghaddam, H. Z. Boeini, Synlett, 10, 1612 (2005). 19 L. Racane, V. Tralic-Kulenovic, D. W. Boykin and G. Karminski-Zamola, Molecules, 8, 342 (2003). 20a T. Itoh, K. Nagata, H. Ishikawa and A. Ohsawa, Heterocycles, 63, 2769 (2004); b T. Itoh, K. Nagata, H. Ishikawa and A. Ohsawa, Heterocycles, 62, 197 (2004); c T. Itoh, K. Nagata, H. Ishikawa and A. Ohsawa, Heterocycles, 52, 1037 (2000). 21 B. C. Ranu, R. Jana and S. S. Dey, Chem. Lett., 33, 274 (2004). 22 D. N. Nicolaides, K. C. Fylaktakidou, K. E. Litinas, G. K. Papageorgios and D. I. Hadjipaviou-litina, J. Heterocycl. Chem., 35, 619 (1998). 23 V. I. Cohen, J. Heterocycl. Chem., 16, 13 (1979). 24a S. D. Joshi and R. N. Usgaonkar, Indian J. of Chem. Sec. B, 21, 399 (1982); b K. Ito and J. Maruyama, Chem. Pharm. Bull., 34 (1) 390 (1986); c U. C. Mashelkar and A. A. Audi, Journal of Indian Council of Chemists, 18 (1), 37 (2001); d K. Ito and N. Kaoru, J. Heterocycl. Chem. 25, 511 (1988). Citing Literature Volume43, Issue5September/October 2006Pages 1367-1369 ReferencesRelatedInformation